Everywhere We Go captured Kenny Chesney in a state of flux. For his first three albums, Chesney mostly brought the New Traditionalist vibe of Alan Jackson and George Strait into a mid-’90s context, making his presence felt on the country charts in the process. But when he started expanding his sound in a more pop-friendly direction on 1997’s I Will Stand, he experienced an uptick in popularity. Everywhere We Go embraces that shift with both arms while simultaneously setting the scene for Chesney to explore his alternative identity as the Jimmy Buffett of country with his next release. Presaging that burgeoning identity, Chesney gets into summer-getaway imagery over an easygoing groove on “How Forever Feels” and even name-drops the king of trop-rock: “Now I know how Jimmy Buffett feels.” The beach-bum escapism is less overt but undeniably present on the laidback title track, which finds him and his objet d’amour by turns stretched out on a beach blanket in Mexico and together on a deserted island. It all provides plenty of precedent for the hit title track of 2002’s No Shoes, No Shirt, No Problems. And when he gets into an upbeat party tune like the smash “She Thinks My Tractor’s Sexy,” Chesney takes his hand off the honky-tonk throttle in favor of a more country-rock feel. Despite the departure from the trad inclinations of Chesney’s earlier albums, there was enough of a through line in the album’s balladic side and in his vocal delivery overall (not to mention a Randy Travis guest shot on the spiritual ballad “Baptism”) to keep old fans from jumping ship. But Chesney’s embrace of rock and pop influences—which, in the end, was simply where the country mainstream was moving anyway—brought plenty of new admirers in. It gave the singer his first real pop crossover hits, lifting him to a greater level of success than ever before. And in retrospect, Everywhere We Go makes perfect sense as the crucial step leading to the even loftier superstar status Chesney was soon to achieve.